


Try a Little Tenderness

by Jacqualine



Series: Red Jacket Series [8]
Category: Anne of Green Gables - L. M. Montgomery, Anne with an E (TV)
Genre: Alternate Universe - Modern Setting, F/M, Fluff, Red Jacket series, Shirbirt, pretty in pink
Language: English
Status: Completed
Published: 2020-09-13
Updated: 2020-09-13
Packaged: 2021-03-06 19:46:43
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,910
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26444377
Author URL: https://archiveofourown.org/users/Jacqualine/pseuds/Jacqualine
Summary: Gilbert goes thrifting with his best friend.
Relationships: Gilbert Blythe/Anne Shirley
Series: Red Jacket Series [8]
Series URL: https://archiveofourown.org/series/1863106
Comments: 6
Kudos: 113





	Try a Little Tenderness

**Author's Note:**

> Unless I think of something in the future...this will be the last Red Jacket story. Thank you all for your support and love for this series.

"I love thrifting!" Anne exclaimed and Gilbert just laughed. He knew that about her, knew everything she liked, Octobers, powdered donuts, dancing in the rain, getting the last word in an argument and and so many more things, but finding long forgotten gems on the racks, with the added bonus of helping the planet by recycling old clothes was another thing she loved She just liked hunting for some unique sweater, a unique pair of pants or some antique purse. "So many unlimited possibilities. And the history of it, someone wore this, perhaps they loved it, and now I will wear and love it. Who knows what these clothes have seen? History, The fall of the Berlin Wall, JFK's assassination, the Great Depression...the Roaring Twenties...unlimited possibilities." She would make up little stories for the blouse or pants she ended up buying.

They had been good friends since she moved to his small PEI town in grade 7, a fierce little wildcat, who stood up to bullies, injustices and perceived insults. She still displayed her old 70s era metal lunch box, Laura from Little House on the Prairie on it, dented on one side from where his had had caused it to cave in. She hadn't liked the nickname Carrots back then and had smashed it over his head, in retaliation for the cruel nickname. Then she had been doubly furious at him because he "made her ruin her retro lunch box". Eventually she forgave him and they spent a lot of their time together, him hopelessly in love with her and her oblivious to his adoration. 

Sometimes it hurt, to be so ridiculously in love with her, to never be brave enough to tell her. He had resigned himself to the friendzone and figured any of her affection was better than none. So he lived for each moment she smiled at him, hugged him or touched his arm...like a dog begging for scraps.

"Are you here for anything specifically? Prom?" He asked, he had been trying to work up the courage to ask her. He thought asking her to go as friends for a laugh would be the best way...but so far he hadn't managed to find his balls long enough to ask.

"I will be keeping an eye out for something for prom. Marilla says we can pull a Pretty in Pink if I see a fabric or style I like."

"Pretty in Pink?" He knew it was an old 80s movie that Anne and her adoptive mother always watched. She once roped him into watching and he had spent the entire time uncomfortable with the idea of being a Duckie...forever in the friendzone even though he was the better choice for Molly Ringwald's character.

"Remember she took her mom's old prom dress and turned it into something cute and fashionable?"

"Oh yeah." He mostly remembered that Duckie got left at the prom while the rich asshole got the girl. That was a bad sign.

"I'm looking for some new jeans, Cole said he would paint something on the leg for me."

"What will he paint? Flowers?"

"Flowers do sound nice..." She pondered. "No I think I am going to get Michael Scott, from the office."

He burst out laughing...of course she would, that was so Anne. The words I love you were on the tip of his tongue, he swallowed them down and steered her toward the racks of denim. "You could get him to do a matching jean jacket...perhaps Prison Mike on the back."

"I love Prison Mike." She exclaimed and began perusing the jeans. His job was to say yes or no to things she held up, most of the time she accepted his opinion but occasionally a questionable orange monstrosity would make the pile, he also held the pile.

"Am I here as a friend and fashion guru or your workhorse?" He asked, four or five pair of jeans in his arms.

"Oh it's cute that you think you are a fashion guru."

"Hey...I know fashion." He responded.

"Really?" She asked with a raised eyebrow. "Okay, go find an outfit, in here."

"Is that a dare?" He asked, feeling a rush of excitement.

"Sure."

"What do I get if I am successful?"

"Oh..uhm...whatever you want." She said. He knew she meant like going to a movie, or fishing, but he felt a thrill, what would she say if he asked for a kiss?

"Deal." He dropped her pile of jeans on a chair nearby and ran off to the men's section.

While he was rifling through the racks he found a few things he thought she would like so he added them to his own pile. He was constantly lifting his head and looking for her, making sure she didn't come over and see his outfit before he could fully assemble it. He would see her red hair across the shop, a shining beacon that he always could count on to find her in a crowd. She lifted her head to look for him at one point and they locked eyes, he felt his breath catch, how could someone be so beautiful and not be aware of it?

"How's it going?" She asked.

"Brilliant. Almost done."

"Really?" She drawled out. "So then when you are ready, you go into the change room and put it on and do a little fashion show for me." He felt his stomach clench in knots, what if she laughed and thought he looked stupid? 

"Sounds great." He lied. He thought he would just have to show her it all matched up, not on his actual body.

"I'm finished, I'll just go into the changeroom now." he told her.

"I can't wait." She exclaimed, and began making her way over to the change room, sitting in a hard plastic chair, a pile of clothes in her lap.

He went over too and showed the clothes to the attendant, she led him to a room and went in and locked the door. His hands trembling he pulled his sweatshirt off, then his T shirt, kicked off his shoes and took a breath before undoing his jeans, glancing at the mirror and remembering the time Moody told him that every change room had a two way mirror with an employee on the other side watching you change, in case you attempted to steal. Gilbert knew it wasn't true but for a second imagined someone was there, watching and judging him. 

"Hurry up Gilbert!" Anne called out to him and he shoved his jeans down and hung them on the spare hook in the change room. Grabbed the pants on the hanger and put them on, they were just plain black dress pants, a bit too long for him but he rolled them up so they came above his ankles, then he put on the dress shirt he had found on the racks. It was loud, red and purple shapes overlapping on a blue background, he had found a suit vest, it was bright and gaudy as well, dark grey with blue and pink paisley print. On top of all that he put the suit jacket he had found, it was burgundy with wide shoulders and shoulder pads to give even more width. He popped the collar of his dress shirt, ran his hands through his hair and sent a silent prayer that she wouldn't laugh too hard at him. 

"I'm ready." He said to her.

"Come out then, I can't wait to see it."

"Okay..." He stalled for a moment longer before turning the lock and opening the door. Her eyes grew wide when she saw him, her mouth dropping open for a second before stretching into the widest smile he had ever seen her wear.

"Oh my God...you look exactly like Duckie Dale." She exclaimed, clapping. She twirled her finger, signing for him to turn around so she could see it all and he did, his heart pounding. She liked it.

"I saw the jacket and the vest, and you had just mentioned Pretty in Pink..." He started to explain.

"You did this on purpose?" She asked him. 

"Well...yeah." He watched her stare at him, her eyes flicking up and down his body, he saw her swallowing several times before spoke.

"I love it." She said. "You make a perfect Duckie."

He felt like he just took a kick to the gut. Forever friendzoned Duckie...and Gilbert was perfect for him. "Thanks. I should go change I guess."

"Are you going to buy it? The clothes."

"I wasn't...no. Should I?"

"I would be a great costume...you look...cute."

She thought he looked cute? It wasn't handsome, hot or sexy, cute was for kittens and puppies. But the way she had smiled at him, he had to buy it. He turned to go back to the changeroom.

"So you won the bet...what do I have to do? Embarrassing selfie? Pop rocks and coke?" He was about to tell her she had to buy lunch but something told him to go big. It was now or never. He turned back around and looked into her eyes.

"Go to prom with me." He blurted out. "Not as a joke, not because no one else asked, not as friends, not because of a dare. Go with me because there is no one else I want to dress up for, dance with and spend the most memorable night of our teen years with." Her eyes were huge again, no smile adorned her face, shock did. He had royally fucked it. 

He spun around, not waiting for her answer and practically ran to the changeroom, leaning his forehead against the door once closed and locked. "Fuck me." He whispered. He started to remove the clothes.

"I'm just going to try a few things on." She said softly...almost hesitantly to him.

"Alright." He answered, he had broke it, he had shot his shot and he had missed badly. Would they ever be natural around each other again? He took his time changing back into his clothes, hanging each item back on it's hanger and then opened the door to the changeroom.

He jumped in surprise because Anne was directly outside the door waiting for him. In a truly hideous yellow dress. It had ruffle going up from the leg to the neckline, sparkles, and for some reason a green rose on one shoulder strap. 

"I always thought that Andi should have been with Duckie at the end of Pretty in Pink. He was her best friend, knew her better than anyone, protected her, encouraged her, cherished her and would have died slaying dragons for her." She reached up a hand and played with his hair for a moment. "I would love to go to prom with you. Not as a joke, not because no one else has asked me, not as friends, not on a dare, but because there is no one else I want to dress up for."

She was saying yes, he understood that part, but the pounding of his blood in his ears was making it difficult to understand the rest. 

"Gilbert, I have dreamed of going to prom with you since grade seven."

And then there was nothing left to do but kiss her. And he did, until the change room attendant told them to knock it off.

**Author's Note:**

> Gilbert is Duckie. I don't know if it has been done before in this universe, I have a vague recollection of reading something about Gilbert being a Duckie, no disrespect if it has been done.
> 
> Title comes from the movie where Duckie dances and lip syncs to the song Try a Little Tenderness by Otis Redding.


End file.
